GB930295A - Benzamide compounds and methods for their production - Google Patents
Benzamide compounds and methods for their productionInfo
- Publication number
- GB930295A GB930295A GB2992660A GB2992660A GB930295A GB 930295 A GB930295 A GB 930295A GB 2992660 A GB2992660 A GB 2992660A GB 2992660 A GB2992660 A GB 2992660A GB 930295 A GB930295 A GB 930295A
- Authority
- GB
- United Kingdom
- Prior art keywords
- general formula
- halo
- acid
- lower alkyl
- prepared
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises: compounds of general formula <FORM:0930295/IV(a)/1> wherein Hal is bromine or chlorine and R1 and R2 are hydrogen atoms or lower alkyl groups, the term "lower" indicating the presence of fewer than 4 carbon atoms; processes for their production (1) by reaction of a compound of general formula <FORM:0930295/IV(a)/2> wherein X is a halogen atom, with a lower alkyl primary amine, (2) by reaction of a compound of general formula <FORM:0930295/IV(a)/3> with a compound of general formula <FORM:0930295/IV(a)/4> (when R1 is H and R2 is identical with "lower alkyl") (3) by reaction of an acyl halide of general formula <FORM:0930295/IV(a)/5> with a lower alkyl primary amine, and (4) by treatment of a 4-halo-3-sulphamoylbenzamide of general formula <FORM:0930295/IV(a)/6> with an alkali metal base and a reactive lower alkyl ester of an inorganic acid or an organic sulphonic acid; and pharmaceutical compositions containing the products or their non-toxic alkali or alkaline-earth metal salts. Sulphonic halides of general formula (II) above are prepared by treating a 4-halobenzamide of general formula <FORM:0930295/IV(a)/7> with two more equivalents of a halosulphonic acid at 100-150 DEG C. 4-Halo-3-(loweralkylsulphamoyl)-benzoyl halides of general formula (III) above are prepared by heating a 4-halobenzoic acid with chlorosulphonic acid to obtain a 4-halo-3-chlorosulphonylbenzoic acid, reacting this with a lower alkyl primary amine, and treating the resulting 4-halo-3-(lower-alkylsulphamoyl)-benzoic acid with an inorganic acid halide (e.g. thionyl chloride, phosphorus tribromide or phosphorus oxychloride). 4-Halo-3-halosulphonylbenzoyl halides of general formula (V) above are prepared by treating a 4-halo-3-halosulphonylbenzoic acid with an inorganic acid halide. 4-Halo-3-sulphamoylbenzamides of general formula (VI) above are prepared by reacting a compound (II) with ammonia. The pharmaceutical compositions, which have diuretic activity, may be in forms suitable for oral or parenteral administration, e.g. tablets, capsules, powders, and aqueous or non-aqueous suspensions and solutions.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83806159A | 1959-09-04 | 1959-09-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB930295A true GB930295A (en) | 1963-07-03 |
Family
ID=25276145
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2992660A Expired GB930295A (en) | 1959-09-04 | 1960-08-30 | Benzamide compounds and methods for their production |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE594699A (en) |
| CH (1) | CH395052A (en) |
| DE (1) | DE1158957B (en) |
| ES (1) | ES260505A1 (en) |
| GB (1) | GB930295A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19953775A1 (en) | 1999-11-09 | 2001-05-10 | Bayer Ag | Active ingredient combinations with insecticidal and acaricidal properties |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB576306A (en) * | 1942-05-05 | 1946-03-28 | Geigy Ag J R | Manufacture of monoazo dyestuffs, capable of being chromed |
| DE960197C (en) * | 1954-11-30 | 1957-03-21 | Bayer Ag | Process for the preparation of 2-chlorobenzoic acids substituted in the 4-position by a sulfonic acid dialkylamide group |
-
1960
- 1960-08-20 ES ES0260505A patent/ES260505A1/en not_active Expired
- 1960-08-30 GB GB2992660A patent/GB930295A/en not_active Expired
- 1960-09-02 CH CH992560A patent/CH395052A/en unknown
- 1960-09-02 BE BE594699A patent/BE594699A/en unknown
-
1963
- 1963-09-02 DE DEP25628A patent/DE1158957B/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE1158957B (en) | 1963-12-12 |
| CH395052A (en) | 1965-07-15 |
| BE594699A (en) | 1961-03-02 |
| ES260505A1 (en) | 1961-04-01 |
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